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Pirates, and the Eternal Sea.

A Pirate’s Pirate: Jimmy Buffett Lessons from the Far Side of Paradise

Life is a daring adventure or nothing at all. When Helen Keller spoke those words, it’s not likely she was thinking of pirates, but they fit perfectly the happiest pirate this side of Margaritaville and his parrothead followers.

If there are three trademarks of a pirate, it’s these

1. The willingness to take bold chances.

2. The willingness to steal.

3. The thirst for adventure.

If this is true, then Jimmy Buffett is not only a pirate’s pirate, but he’s had school in session for over forty years, teaching parrothead/pirates the intimate details of how to pull this pirate thing off. Let’s get started by putting a few things up front.

Jimmy’s been shot down in Jamaica, crashed his plane in Long Island, been put down by critics, thrown out of sports arenas, and had his share of illicit taxi rides. Yet each time cannon balls fly his way, he’s found a way to “… jump up and smile back at …” us.

This is exactly what makes Jimmy Buffett a pirate’s pirate. Adversity is no stranger to him. It’s just that he’s learned to make friends with it. It’s hard to know whether Jimmy shines because of his resilience, or whether his resilience comes from his ability to shine. I’m convinced if given an electric guitar and Jimmy Buffett‘s example, Blackbeard would have turned out differently.

Let’s face it. No one would ever accuse Jimmy of being a saint, yet there are few people I know closer to God. When you make so many people happy in a world writhing in pain, it’s one of the most godlike things a human can do. More of us should learn to do that.

As for this whole stealing thing, Jimmy is guilty. For over forty years, he’s stolen our hearts while encouraging us to live our dreams. What‘s more, he’s taught us to steal our lives and our dreams back from those who stole them from us a piece at a time.

Though he seems to preach a hedonistic lifestyle, Jimmy is more of a Buddha than a sensualist. It’s all about the present moment. No matter what you were expecting, it is always now. Breathe in, breathe out. Move on. It’s a terrific lesson.

And whoever heard of a pirate who played it safe, or backed down from an adventure? From the very start, Jimmy’s encouraged us to step outside our comfort zone and join him on the gangplank where both danger and fun await. Who knows what incredible things we’ll discover not only on the far side of the world but within ourselves when we dare to go for our dreams?

Jimmy’s also taught us all work and no play makes for a dull and very cranky pirate. Like Blackbeard who had Port Royal for a refuge, he’s taught us to find that special retreat where we can restore our pirate souls. That particular harbor can be as close as the hammock in our backyard or an island half a world away.

One more thing Jimmy has reminded us of over the years is the need to stay in touch with the simple things in life. A tin cup chalice holds wine as well as a golden one. Oysters and beer are as filling as a gourmet dinner. Watching the sun set, listening to the waves break on the shore, sharing a smile with a friend are not expensive but they are priceless.

What pirate doesn’t know S*** happens! Cannonballs fly. Volcanoes rain down hot lava, and hurricanes blow us off course. Every day we encounter sons-of-bitches and lose some of our riches. Yet through it all, Jimmy has taught us  it’s important not to misplace our smile or lose our sense of humor.

Moreover, Jimmy has awakened us to the fact that we’re going to find Gypsies in the Palace. We’re going to run into our share of Fruitcakes. People will disappoint you. They’ll betray you. Accept it, but don’t let them steal your pirate heart.

Finally, Jimmy taught us to recognize our gifts, to be who we were meant to be. Being a naval academy grad or a Jesuit priest is not good enough if your pirate heart calls you to be the twelve-volt man. What’s your particular gift? Are you using it or are you just treading water?

I’m asking you whether you’re a sailor or the son of a son of a sailor, do one thing this coming week that will speak to the Pirate in you, the Adventurer that’s not afraid to hoist his anchor and set his sails. There’s a big ocean out there where the Island of your Dreams lies. What are you waiting for?

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